Notable Partners: Kelly LeBrock, Georgiana Carter, Mimi Manchu, Susan Anspach, Angelica Houston, Winnie Hollman, Rebecca Broussard, Julie Delpy, Lara Flynn Boyle, Kate Moss

What else is there to say about this king? He's a Hollywood OG who, in the downtime between a handful of iconic roles and posting up courtside at every Lakers game—usually in all-black-everything—has slayed half of old Hollywood, rarely ever settling down. His last two notable girlfriends were Lara Flynn Boyle and Kate Moss in the early aughts, i.e. his early 60s. Dude was pulling models even after he graduated from his casual wear youth to his cozy boy but still fresh old age. Swag Lord Extraordinaire.